Benzyl chloroformate → HCID 19358329, compound

HRID 576623Notes

Reaction equation

HRID 576623 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][NH:6][CH2:5]2.C(N(CC)C(C)C)(C)C.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[CH2:5]2

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 147958715-Bromoisoindoline

Product 1

HCID 19358329HCID 19358329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 5-bromoisoindoline (1.1 g, 5.5 mmol) in dichloromethane (15 mL) was added N,N-diisopropylethylamine (1.16 mL, 6.6 mmol) followed by benzyl chloroformate (942 μL, 6.6 mmol). The cold bath was removed and stirring continued for 2 hr. The reaction mixture was then diluted with dichloromethane, washed with water, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by silica chromatography (25 g silica eluted with 0-50% ethyl acetate in hexane) to give the title compound as a white solid.

Workup

  1. customThe cold bath was removed
  2. additionThe reaction mixture was then diluted with dichloromethane
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica chromatography (25 g silica eluted with 0-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-87439bb8ed8e41009a3be8bce6a50763
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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